Dimethyl Sulfoxide → HCID 57455395, compound

Participants

Reaction Steps

Oxalyl chloride (4.99 mL, 57.28 mmol) was added to a mixture of methyl sulfoxide (DMSO) (5.54 g, 71.46 mmol) in dichloromethane (50 mL) at −78° C. and stirred for 5 minutes. 5-(2-Propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-ol (14.2 g, 47.74 mmol) was added dropwise, followed by the addition of triethylamine (19.96 mL, 143.2 mmol). The reaction was allowed to warm to ambient temperature and the reaction was stirred for 2 hours. Saturated aqueous sodium bicarbonate solution was added and the layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, filtered over magnesium sulfate, and concentrated under reduced pressure to afford 10.7 g of 5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one as a brown oil.

Provenance & Evidence